This invention relates to novel (aminosulfonyl)pyridinecarboxamides. The compounds of this invention and their agriculturally suitable salts are useful as agricultural chemicals, and in particular, as herbicides which may be selective to corn.
U.S. Pat. No. 4,544,401 and U.S. Pat. No. 4,435,206 disclose herbicidal pyridinesulfonylureas.
U.S. Pat. No. 4,518,776 (Swiss priority 7/19/82) and EP-A-No. 101,670 (Swiss priority 8/23/82, published 2/29/84) disclose, in part, a process for the preparation of compounds of formula ##STR1## R.sub.1 is, among other values, C(O)NHC.sub.1 -C.sub.4 alkyl or C(O)N(C.sub.1 -C.sub.4 alkyl).sub.2 ;
R.sub.2 is H, halogen, CF.sub.3, NO.sub.2, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; PA0 A is O, S, NR.sub.5 or --C.dbd.N--; PA0 X is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylamino or di-C.sub.1 -C.sub.4 alkylamino; PA0 Y is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy; and PA0 Z is CH or N. PA0 R.sub.8 is H, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 cyanoalkyl, OCH.sub.3, OC.sub.2 H.sub.5 or C.sub.3 -C.sub.5 alkenyl; PA0 R.sub.9 is H, C.sub.1 -C.sub.5 alkyl or C.sub.3 -C.sub.5 alkenyl; PA0 Y is O, S or C(R.sub.6).dbd.N; PA0 R.sub.a is H, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 haloalkyl, C.sub.1 -C.sub.5 alkoxy, C.sub.1 -C.sub.5 haloalkoxy, C.sub.1 -C.sub.5 alkylthio, C.sub.2 -C.sub.10 alkoxyalkyl or C.sub.2 -C.sub.10 alkoxyalkoxy; PA0 R.sub.b is the same as R.sub.a or NR.sub.c R.sub.d ; and PA0 E is CH or N. PA0 Y is O or S; PA0 Z is O or S; PA0 E is N or CH; PA0 R.sub.1 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkoxy, halogen, C.sub.1-C.sub.4 alkylthio, NR.sub.6 R.sub.7 or alkoxyalkyl containing not more than 4 carbon atoms; PA0 R.sub.2 is, among others, CONR.sub.6 R.sub.7 ; PA0 R.sub.3 is H, halogen, C.sub.1 -C.sub.3 alkyl, OCH.sub.3 or CF.sub.3 ; PA0 R.sub.5 is H, NO.sub.2, F, Cl, Br, CH.sub.3, CF.sub.3, S(O).sub.n C.sub.1 -C.sub.3 alkyl, COC.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.3 alkoxy; PA0 R.sub.6 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 cyanoalyl, methoxy or ethoxy; and PA0 R.sub.7 is H, C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 alkenyl. PA0 R.sub.5 is H, CH.sub.3, Cl, Br, CO.sub.2 R.sub.15, C(O)NR.sub.16 R.sub.17, SO.sub.2 NR.sub.16 R.sub.17, SO.sub.2 N(OCH.sub.3)CH.sub.3, SO.sub.2 R.sub.18 or NO.sub.2 ; PA0 R.sub.16 is C.sub.1 -C.sub.2 alkyl; PA0 R.sub.17 is C.sub.1 -C.sub.2 alkyl PA0 R.sub.19 is CH.sub.3, Cl, Br, NO.sub.2, C.sub.1 -C.sub.2 alkylthio or C.sub.1 -C.sub.2 alkylsulfonyl; PA0 X is CH.sub.3, OCH.sub.3, Cl, Br, OCH.sub.2 CF.sub.3 or OCHF.sub.2 ; PA0 Y is C.sub.1 -C.sub.3 alkyl, CH.sub.2 F, cyclopropyl, C.tbd.CH, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, OCH.sub.2 CH.sub.2 F, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CF(OCH.sub.3).sub.2, ##STR5## CR(OCH.sub.2 CH.sub.3).sub.2 or OCF.sub.2 H; and Z is CH or N. PA0 R.sub.2 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.2 alkoxy; or PA0 R.sub.1 and R.sub.2 may be taken together to form --(CH.sub.2).sub.n --, wherein n is 2, 3 or 4; PA0 R.sub.3 is H, Cl, F, Br, CH.sub.3, CF.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, OCF.sub.2 H, SCH.sub.3, SCH.sub.2 CH.sub.3, SCF.sub.2 H, NHR.sub.4 or NR.sub.4 R.sub.5 ; PA0 R.sub.4 is CH.sub.3 or CH.sub.2 CH.sub.3 ; PA0 R.sub.5 is CH.sub.3, CH.sub.2 CH.sub.3, OCH.sub.3 or OCH.sub.2 CH.sub.3 ; and PA0 X is CH.sub.3, CH.sub.2 F, CH.sub.2 CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl or CH.sub.2 OCH.sub.3. PA0 (1) Compounds of Formula I where R is H. PA0 (2) Compounds of Preferred 1 where J is J-1. PA0 (3) Compounds of Preferred 1 where J is J-2. PA0 (4) Compounds of Preferred 1 where J is J-3. PA0 (5) Compounds of Preferred 1 where J is J-4. PA0 (6) Compounds of Preferred 2 where X is OCH.sub.3, CH.sub.3 or Cl. PA0 (7) Compounds of Preferred 6 where R.sub.3 is H, F, Cl, OCH.sub.3, N(CH.sub.3).sub.2 or SCH.sub.3. PA0 (8) Compounds of Preferred 7 where R.sub.1 is H or CH.sub.3 ; and R.sub.2 is CH.sub.3, CH.sub.2 CH.sub.3 or OCH.sub.3. PA0 (9) Compounds of Preferred 3 where X is OCH.sub.3, CH.sub.3 or Cl. PA0 (10) Compounds of Preferred 9 where R.sub.3 is H, F, Cl, OCH.sub.3, N(CH.sub.3).sub.2 or SCH.sub.3. PA0 (11) Compounds of Preferred 10 where R.sub.1 is H or CH.sub.3 ; and R.sub.2 is CH.sub.3, CH.sub.2 CH.sub.3 or OCH.sub.3. PA0 (12) Compounds of Preferred 4 where X is OCH.sub.3, CH.sub.3 or Cl. PA0 (13) Compounds of Preferred 12 where R.sub.3 is H, F, Cl, OCH.sub.3, N(CH.sub.3).sub.2 or SCH.sub.3. PA0 (14) Compounds of Preferred 13 where R.sub.1 is H or CH.sub.3 ; and R.sub.2 is CH.sub.3, CH.sub.2 CH.sub.3 or OCH.sub.3. PA0 (15) Compounds of Preferred 5 where X is OCH.sub.3, CH.sub.3 or Cl. PA0 (16) Compounds of Preferred 15 where R.sub.3 is H, F, Cl, OCH.sub.3, N(CH.sub.3).sub.2 or SCH.sub.3. PA0 (17) Compounds of Preferred 16 where R.sub.1 is H or CH.sub.3 ; and R.sub.2 is CH.sub.3, CH.sub.2 CH.sub.3 or OCH.sub.3.
U.S. Pat. No. 4,518,776 generically discloses but does not claim compounds of the invention. (No pyridine carboxamides are specifically disclosed.)
U.S. Pat. No. 4,521,597 discloses, in part, a process for the preparation of compounds of formula ##STR2## R.sub.3 is H, halogen, NO.sub.2, OCH.sub.3 or CF.sub.3 ; R.sub.5 is, among others, CONR.sub.8 R.sub.9 ;
This application generically discloses but does not claim compounds of the invention. (No pyridine carboxamides are specifically disclosed.)
U.S. Pat. No. 4,549,898 discloses herbicidal sulfonylureas of formula ##STR3## wherein X is O, S, NR.sub.4 or C(R.sub.5)=N;
EP-A-No. 155,767, published 9/25/85, discloses, in part, herbicidal sulfonylureas of formula ##STR4## wherein R is H or CH.sub.3 ;
Despite the existence of these materials, there is still a need for improved agricultural chemicals, especially herbicides which may be selective for corn. According to this invention, such herbicides have unexpectedly been found.